TY - JOUR
T1 - The Biginelli Reaction Is a Urea-Catalyzed Organocatalytic Multicomponent Reaction
AU - Puripat, Maneeporn
AU - Ramozzi, Romain
AU - Hatanaka, Miho
AU - Parasuk, Waraporn
AU - Parasuk, Vudhichai
AU - Morokuma, Keiji
N1 - Publisher Copyright:
© 2015 American Chemical Society.
PY - 2015/7/17
Y1 - 2015/7/17
N2 - The recently developed artificial force induced reaction (AFIR) method was applied to search systematically all possible multicomponent pathways for the Biginelli reaction mechanism. The most favorable pathway starts with the condensation of the urea and benzaldehyde, followed by the addition of ethyl acetoacetate. Remarkably, a second urea molecule catalyzes nearly every step of the reaction. Thus, the Biginelli reaction is a urea-catalyzed multicomponent reaction. The reaction mechanism was found to be identical in both protic and aprotic solvents. (Chemical Presented)
AB - The recently developed artificial force induced reaction (AFIR) method was applied to search systematically all possible multicomponent pathways for the Biginelli reaction mechanism. The most favorable pathway starts with the condensation of the urea and benzaldehyde, followed by the addition of ethyl acetoacetate. Remarkably, a second urea molecule catalyzes nearly every step of the reaction. Thus, the Biginelli reaction is a urea-catalyzed multicomponent reaction. The reaction mechanism was found to be identical in both protic and aprotic solvents. (Chemical Presented)
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U2 - 10.1021/acs.joc.5b00407
DO - 10.1021/acs.joc.5b00407
M3 - Article
AN - SCOPUS:84937239664
SN - 0022-3263
VL - 80
SP - 6959
EP - 6967
JO - Journal of Organic Chemistry
JF - Journal of Organic Chemistry
IS - 14
ER -